That was so fun to read.

Funny

Cute...I loved the whole Judy thing...

This kinda reminds me of a fic I was reading on another fandom before it was apparently abandoned 2 years ago. It was an AU based off another show just using the characters but not the situations of the show. Basically in it this guy became best friends with his neighbor who was 5 years older (their brothers were dating too) after they had no one else to hang out with. Eventually they fell for each other but they kept it to themselves for a few reasons such as not wanting to ruin the older boy's reputation (he was in college while the younger was about to go into his senior year of high school), he could get in trouble for dating someone so much younger, they wanted to make sure they were going somewhere before telling anyone, they didn't want to have to explain their sexuality (before they fell for each other both only liked women so it would get complicated) and they knew their families likely wouldn't approve. Not because they were both guys (afterall their brothers were dating each other) but because of the age difference. Their siblings noticed the feelings between them and teased them about it a lot but they claimed there was nothing there. Then they gave each other a hickey and the older boy came downstairs without a shirt for breakfast and had an INTERESTING time explaining that to his siblings. They decided to maintain a long-distance relationship because they cared about each other too much to break up at summer's end but at the end of the last real chapter (the last one posted was a series of emails between them) the older boy decided he couldn't leave without a proper goodbye and promptly kissed his boyfriend in front of all their siblings. In the emails chapter it was mentioned they didn't take THAT well but it was never shown how that showdown went. A girl who was interested in the younger boy pushed him for a date as did his friends and his boyfriend told him to go since he trusted him enough for that and he couldn't reject the date without explaining everything to his friends. At the end of the night the girl proved to be like Taylor and when he wouldn't kiss her realized he liked someone else and told him the person was lucky.

I like how you made it different with Connor's dad knowing instead of the moms.
Update soon